New synthetic routes to azacarborane clusters: Nitrile insertion reactions of nido-5,6-C2B8H11- and nido-B10H13-

Journal of the American Chemical Society

Volumn 118, Issue 27, 1996, Pages 6407-6421

  Wille, Andrew E ^a   Su, Kai ^a   Carroll, Patrick J ^a   Sneddon, Larry G ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBORON DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029885057     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960787m     Document Type: Article

References (69)

1. (a) Hertler, W. R.; Klanberg, F.; Muetterties, E. L. Inorg. Chem. 1961, 6, 1696-1706.
2. (b) Baše, K.; Plešek, J.; Heřmánek, S. J. Chem. Soc., Chem. Commun. 1975, 934-935.
3. (c) Plešek, J.; Heřmánek, S.; Huffman, J.; Ragatz, P.; Schaeffer, R. J. Chem. Soc., Chem. Commun. 1975, 935-936.
4. (d) Štíbr, B.; Baše, K.; Plešek, J., Heřtnánek, S.; Dolanský, J.; Janoušek, Z. Pure Appl. Chem. 1977, 49, 803-811.
5. (e) Base, K.; Štíbr, B.; Zakharova, I. A. Synth. React. Inorg. Met.-Org. Chem. 1980, 10, 509-514.
6. (f) Bicerano, J.; Lipscomb, W. N. Inorg. Chem. 1980, 19, 1825-1827.
7. (g) Dolansky, J.; Heřmánek, S.; Zahradnik, R. Collect. Czech. Chem. Commun. 1981, 46, 2479-2493.
8. (h) Baše, K.; Hanousek, F.; Plešek, J.; Štíbr, B. J. Chem. Soc., Chem. Commun. 1981, 1162-1163.
9. (i) Baše, K. Collect. Czech. Chem. Commun. 1983, 48, 2593-2603.
10. (j) Todd, L. J.; Arafat, A.; Baer, J.; Huffman, J. C. Mol. Struct. Energ., Adv. Boron Boranes 1986, 5, 287-295.
11. (k) Arafat, A.; Baer, J.; Huffman, J. C.; Todd, L. J. Inorg. Chem. 1986, 25, 3757-3761.
12. (l) Boese, R.; Kröckert, B.; Paetzold, P. Chem. Ber. 1987, 120, 1913-1915.
13. (m) Küpper, S.; Paetzold, P. Chem. Ber. 1989, 122, 479-480.
14. (n) Štíbr, B.; Kennedy, J. D.; Jelínek, T. J. Chem. Soc., Chem. Commun. 1990, 1309-1310.
15. (o) Müller, J.; Paetzold, P.; Boese, R. Heteroat. Chem. 1990, 1, 461-465.
16. (p) Müller, J.; Runsink, J.; Paetzold, P. Angew. Chem., Int. Ed. Eng. 1991, 30, 175.
17. (q) Zahradnik, R.; Balaji, V.; Michl, J. J. Comput. Chem. 1991, 12, 1147-1156.
18. (r) Paetzold, P. Pure Appl. Chem. 1991, 63, 345-350.
19. (s) Nöth, H.; Geisberger, G.; Linti, G.; Loderer, D.; Rattay, W.; Salzbrenner, E. Pure Appl. Chem. 1991, 63, 351-355.
20. (t) Müller, J.; Paetzold, P.; Englert, U.; Runsink, J. Chem. Ber. 1992, 125, 97-102.
21. (u) Meyer, F.; Müller, J.; Paetzold, P.; Boese, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1227-1229.
22. (v) Hnyk, D.; Bühl, M.; Schleyer, P. v. R.; Volden, H. V.; Gundersen, S.; Müller, J.; Paetzold. P. Inorg. Chem. 1993, 32, 2442-2445.
23. (w) Meyer, F.; Müller, J.; Schmidt, M. U.; Paetzold, P. Inorg. Chem. 1993, 32, 5053-5057.
24. (x) Jelínek, T.; Kennedy, J. D.; Štíbr, B. J. Chem. Soc., Chem. Commun. 1993, 1628-1629.
25. (y) Paetzold, P.; Müller, J.; Meyer, F.; Hansen, H-P.; Schneider, L. Pure Appl. Chem. 1994, 66, 255-262.
26. (z) Jélínek, T.; Kennedy, J. D.; Štíbr, B. J. Chem. Soc., Chem. Commun. 1994, 677-678.
27. (aa) Roth, M.; Paetzold, P. Chem. Ber. 1995, 128, 1221-1224.
28. (bb) Lomme, P.; Meyer, F.; Englert, U.; Paetzold, P. Chem. Ber. 1995, 128, 1225-1229.
29. (a) Kester, J. G.; Huffman, J. C.; Todd, L. J. Inorg. Chem. 1988, 27, 4528-4532.
30. (b) Baše, K.; Bown, M.; Fontaine, X. L. R.; Greenwood, N. N.; Kennedy, J. D.; Štíbr, B.; Thormon-Pett, M. J. Chem. Soc., Chem. Commun. 1988, 1240-1241.
31. (c) Nestor, K.; Fontaine, X. L. R.; Kennedy, J. D.; Štíbr, B.; Baše, K.; Thornton-Pett, M. Collect. Czech. Chem. Commun. 1991, 56, 1607-1617.
32. Plešek, J.; Štíbr, B.; Heřmánek, S. Chem. Ind. (London) 1974, 662-663.
33. Janoušek, Z.; Fusek, J.; Štíbr, B. J. Chem. Soc., Dalton Trans. 1992, 2649-2650.
34. Holub, J.; Jelinek, T.; Plešek, J.; Štíbr, B.; Heřmánek, S.; Kennedy, J. D. J. Chem. Soc., Chem. Commun. 1991, 1389-1390.
35. Kang, S. O.; Furst, G. T.; Sneddon, L. G. Inorg. Chem. 1989, 28, 2339-2347.
36. Shriver, D. F.; Drezdzon, M. A. Manipulation of Air Sensitive Compounds, 2nd ed., Wiley: New York, 1986.
37. Plešek, J.; Heřmánek, S. Collect. Czech. Chem. Commun. 1974, 39, 821-826.
38. Plumb, C. A.; Sneddon, L. G. Organometallics 1992, 11, 1681-1685.
39. Kang, S. O.; Carroll, P. J.; Sneddon, L. G. Organometallics 1988, 7, 772-776.
40. Chambers, J. Q.; Norman, A. D.; Bickell, M. R.; Cadle, S. H. J. Am. Chem. Soc. 1968, 90, 6056-6062.
41. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation, (1985 and 1992).
42. Frisch, M. J.; Head-Gordon, M.; Trucks, G. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M.; Binkley, J. S.; Gonzalez, C.; Defrees, D. J.; Fox, D. J.; Whiteside, R. A.; Seeger, R.; Melius, C. F.; Baker, J.; Martin, R. L.; Kahn, L. R.; Stewart, J. J. P.; Topiol, S.; Pople, J. A. Gaussian 90, Revision H, Gaussian, Inc.; Pittsburgh, PA, 1990.
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb, M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT, Revision F.2; Gaussian, Inc.: Pittsburgh, PA, 1993.
44. Keller, W.; Barnum, B. A.; Bausch, J. W.; Sneddon, L. G. Inorg. Chem. 1993, 32, 5058-5066.
45. (a) Williams, R. E. Inorg. Chem. 1971, 10, 210-214.
46. (b) Wade, K. Adv. Inorg. Chem. Radiochem. 1976, 18, 1-66.
47. (c) Williams, R. E. Adv. Inorg. Chem. Radiochem. 1976, 18, 67-142.
48. (d) Rudolph, R. W. Acc. Chem. Res. 1976, 9, 446-452.
49. Garrett, P. M.; Ditta, G. S.; Hawthorne, M. F. J. Am. Chem. Soc. 1971, 93, 1265-1266.
50. (a) Reddy, J. van der Mass; Lipscomb, W. N. J. Chem. Phys. 1959, 31, 610-616.
51. (b) Reddy, J. van der Mass; Lipscomb, W. N. J. Am. Chem. Soc. 1959, 81, 754.
52. (c) Sands, D. E.; Zalkin, A. Acta Crystallogr. 1962, 15, 410-417.
53. Kendall, D. S.; Lipscomb, W. N. Inorg. Chem. 1973, 12, 546-551.
54. Onak, T.; Wan, E. J. Magn. Reson. 1974, 14, 66-71.
55. (a) Su, K.; Barnum, B.; Carroll, P. J.; Sneddon, L. G. J. Am. Chem. Soc. 1992, 114, 2730-2731.
56. (b) Su, K.; Carroll, P. J.; Sneddon, L. G. J. Am. Chem. Soc. 1993, 115, 10004-10017.
57. Štíbr, B.; Plešek, J.; Heřmánek, S. Collect. Czech., Chem. Commun. 1973, 38, 338-342.
58. (a) Štíbr, B. Private communication,
59. (b) Holub, J.; Wille, A. E.; Štíbr, B.; Carroll, P. J.; Sneddon, L. G. Inorg. Chem. 1994, 33, 4920-4926.
60. (a) Dickerson, R. E.; Wheatley, P. J.; Howell, P. A.; Lipscomb, W. N. J. Chem. Phys. 1957, 27, 200-209.
61. (b) Simpson, P. G.; Lipscomb, W. N. J. Chem. Phys. 1961, 35, 1340-1343.
62. (c) Beaudet, R. A. In Advances in Boron and the Boranes; Liebman, J. F., Greenberg, A., Williams, R. E., Eds.; VCH Publishers: New York, 1988; pp 417-490.
63. (a) Wang, F. E.; Simpson, P. G.; Lipscomb, W. N. J. Am. Chem. Soc. 1961, 83, 491-492.
64. (b) Wang, F. E.; Simpson, P. G.; Lipscomb, W. N. J. Chem. Phys. 1961, 35, 1335-1339.
65. (a) Greenwood, N. N.; Gysling, H. J.; McGinnety, J. A.; Owen, J. D. J. Chem. Soc., Chem. Commun. 1970, 505-506.
66. (b) Greenwood, N. N.; McGinnety, J. A.; Owen, J. D. J. Chem. Soc., Dalton Trans. 1972, 986-989.
67. (c) Huffman, J. C. Report No. 82210, Indiana University of Chemistry Molecular Structure Center.
68. Schaeffer, R.; Sneddon, L. G. Inorg. Chem. 1972, 11, 3102-3104.
69. Williams, R. E. Chem. Rev. 1992, 92, 177-207 and references therein.